What I'd Tell Myself on Day One

Six years in, the lessons I learned about passion projects, anxiety, and cleanup jobs.

Six years ago this month, I started consulting. I’d left the nonprofit I’d been at for 14 years, COVID was raging, and I hadn’t left my apartment for anything other than a once-a-day walk in months. The vaccines weren’t even on the horizon. I remember pre-grieving the end of public gatherings without masks, wondering whether anything would ever feel normal again. It was a strange time to try something new.

And the anniversary hook is irresistible, so here I am: what would I tell the version of me sitting in that apartment, two months into a pandemic and on the verge of a new career as an independent consultant, if I could go back?

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Write something that isn’t for a client

I was lucky to find consulting work early that met my financial needs without consuming all my time. So I did something I hadn’t planned: I started writing a memoir about my 14 years in nonprofit work: what I’d seen, what I thought the big advocacy organizations were getting wrong, and what I wished I’d done differently. I spent a solid year on it. It ended up at 294 pages with a bibliography spanning over 100 entries.

That manuscript never turned into a book. I never submitted it anywhere or tried to find an agent. After a few trusted friends read it, I realized I didn’t have the stomach or stamina for the revisions it would need.

But the writing changed me in ways the consulting work alone couldn’t. It stretched skills I cared about, and forced me to develop frameworks for thinking about social change that later became central to my client work. And it diversified my professional identity, which I hadn’t been looking for but realized was quite valuable once I obtained it. My old nonprofit job was totalizing in that it took all that I had to give (and more), so when I left, I lost my network, my community, and my whole professional self-worth. Spreading that identity out, which is something consulting already affords but passion projects multiply, has become a must-have for me.

I stumbled into this by dumb luck, but I’ve since learned to maintain it deliberately. This newsletter is now that project for me. It keeps my thinking from getting stale, introduces me to people I wouldn’t otherwise meet, and exercises muscles my client work doesn’t.

The first thing I’d tell myself at year one: keep a passion project in your life. It will make you a better consultant than any amount of additional billable hours.

Speaking of, stop billing by the hour

Sam from 2020 would have replied to the previous piece of advice with a predictable objection: Cool, but how do I make time for a passion project when I need to fill my day with billable hours?

Sam from 2026 would say: stop billing hourly. If you’re tracking your time in 15-minute increments, you will struggle to find financial security or professional success.

I took plenty of hourly contracts back then. I told myself they were a foot in the door, and if I did good hourly work, the client would eventually bring me into something bigger. They didn’t!

Hourly billing, for the kind of work I was doing, slotted me into the hired-help category rather than the strategic-partner one. The client thought of me the way they thought of their accountant: someone who showed up when called and billed for the time. Not someone whose judgment they sought out.

Amy (my partner) told me this from day one. (She is usually right about these things, and I am usually slow to listen, and most of the time she tolerates me.) I’d heard the case for value-based pricing plenty of times before, but I needed to feel the difference in my own practice before I believed it. The contracts where I scoped a deliverable and quoted a project fee were the ones that led to real relationships. The hourly ones just led to clock-watching and restrictions on what I could really do.

The anxiety trap (and watch out for cleanup jobs)

I took pretty much any work I could find in those early days. I’m not sure that was wrong, exactly. Financial security matters to me, and turning down paid work when you’re new feels foolishly optimistic.

But so much of what I took on was stuff I didn’t care about. Worse, the client often didn’t know why they were hiring me, and I couldn’t clearly articulate what I offered that was valuable. I’d find myself caught in a three-way bind: I wanted to do excellent work; I suspected the work itself wasn’t that important; and I knew it probably wasn’t even what the client most needed. That combination produces the awful dread I always have at the start of every new engagement, a tightness I eventually recognized as the feeling of being about to be found out as the wrong person for the job.

I don’t know how to fully solve that dynamic. Earning enough money is bedrock for me. But I would go back and give myself more perspective on it, because those anxiety-riddled early weeks of each new project were genuinely hard, and they didn’t need to be quite so hard.

What I would tell 2020 Sam with conviction: watch out for cleanup jobs. I took an engagement as a fractional CFO with a nonprofit. I thought I’d be helping with financial strategy and planning, which is the kind of work that gets my brain going. Instead, I spent nearly all my time picking up the failed implementation of an ERP system the organization had been paying for but wasn’t even using. I was debugging software adoption, not thinking about strategic planning.

So many projects a consultant gets hired for are some version of this: someone else started it, it stalled or went sideways, and now you’re the person holding the mop. Cleanup stinks. I’m not saying to 2020 Sam never to take those projects, but go in with your eyes open about what you’re actually signing up for. I would also give myself skills in the form of discovery meetings (pre-contract) to ascertain if a cleanup job is lying in wait.

The money I wasted and the time I’ll never get back

My biggest financial regrets are mundane. I used LegalZoom for my corporate setup instead of working with a real lawyer, and it cost me more than it should have plus I couldn’t get answers to basic questions, which led to a series of avoidable mistakes. I paid QuickBooks $25 per invoice for bill pay when a small-business-friendly bank could have done it for free. I bought Adobe subscriptions I didn’t need for e-signatures when simpler free tools existed. In sum, I should have looked harder for free stuff, because all of those expenses came out of my pay.

My time regrets are worse. I started a newsletter early on, but I had no idea how to build an audience. I wrote a few articles that just sat on my website, unread. (And now this newsletter exists, so the instinct was right, even if the execution took years to catch up.)

And the worst time regret is I never—not once in my early engagements—did an intentional end-of-project wrap-up. By the time it occurred to me that I should be collecting testimonials, building case studies, and documenting examples of my work, I had already forgotten the details. I left years of social proof on the table because I was always too focused on the next engagement to properly close the current one. Such a waste!!!

Find your people (even when you can’t leave the house)

I started consulting at the beginning of a pandemic. Traveling or meeting people in person was not realistic. I didn’t know how to build a professional community online. And so I went for a long time with no one to talk to about consulting, by which I mean the experience of doing it. I was by myself wondering if my pipeline would hold and setting my schedule while having no one notice whether I showed up.

I wish I’d figured this out sooner. It took me years to find the communities and relationships that now feel essential to how I work. If I could go back, I’d tell myself to treat building that network with the same urgency I brought to finding clients.

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If I’m looking for a thread that connects all of this, it’s probably something like: the early version of me spent his energy on the wrong things. I optimized for billable hours instead of project fees. I said yes to work that didn’t fit because the money was reassuring. I paid for convenience when patience would have been cheaper. I skipped the relationship-building and the documentation because they didn’t feel urgent.

Everything that actually mattered — the passion project, the pricing model, the community, the wrap-ups — felt like a luxury at the time, but they were the infrastructure.

I’m not sure any amount of advice would have changed my behavior in year one. I probably needed to learn most of this the slow way. But if there’s a version of me somewhere in 2020, sitting in that apartment, reading this on a laptop between walks, I hope he at least takes notes.